Stereoselective Synthesis of (−)-Spicigerolide

descriptionPublicationkeyboard_double_arrow_right Article 05 Feb 2009 Spain English Publisher:American Chemical Society (ACS)Journal:The Journal of Organic Chemistry, volume 74, pages 2,008-2,012 (issn: 0022-3263, eissn: 1520-6904,

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Authors: Georges, Yohan; Ariza Piquer, Xavier; García Gómez, Jordi;

doi: 10.1021/jo8025753

pmid: 19196165

handle: 2445/48632

Stereoselective Synthesis of (−)-Spicigerolide

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Abstract

(-)-Spicigerolide was stereoselectively synthesized from a protected (S)-lactaldehyde. The synthesis of the polyacetylated framework relied on two Zn-mediated stereoselective additions of alkynes to aldehydes as well as a regiocontrolled [3,3]-sigmatropic rearrangement of an allylic acetate. The pyranone moiety was constructed via ring-closing metathesis.

Country

Spain

Related Organizations

University of Barcelona
Spain

Keywords

Síntesi orgànica, Natural products, Estereoquímica, Botànica mèdica, Molecular Conformation, Organic synthesis, Stereoisomerism, Plantes, Plants, Medical botany, Citotoxicitat per mediació cel·lular, Cell-mediated cytotoxicity, Lactones, Stereochemistry, Productes naturals, Càncer, Cancer

5 Research products, page 1 of 1

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